Depart Boston and head north toward Maine’s coastline, trading city streets for ocean air and rocky shores on a smooth, scenic drive.

This paved coastal path stretches along the cliffs of Ogunquit, offering continuous views of the Atlantic, rocky coves, and crashing waves—one of the most celebrated ocean walks in New England.

A classic Maine seaside town, Kennebunkport is known for its historic homes, small shops, and harbor views. It’s an ideal stop to explore at a relaxed pace and soak in coastal charm.

Portland’s Old Port is a lively waterfront district where working lobster boats dock alongside historic brick warehouses. This is the best place to enjoy fresh, locally caught lobster (at your own expense), browse boutiques, and experience the city’s maritime character.

As you pass through the harbor area, you’ll see fishing vessels, sailboats, and waterfront restaurants that highlight Portland’s deep connection to the sea.

The main artery of the Old Port, Commercial Street showcases the energy of Portland’s working waterfront, with shops, markets, and harbor views lining the route.

Maine’s most iconic lighthouse stands at the edge of Fort Williams Park, surrounded by rugged cliffs and sweeping ocean views. It’s a powerful and scenic finale to the day

Return to Boston in the evening, having experienced the coastal towns, landscapes, and maritime culture that define southern Maine